The present invention relates to a chiral transition metal complex, which is useful as a catalyst for converting a prochiral unsaturated organic compound to a corresponding asymmetric compound, and a process for producing the same.
Martins et al. discloses an optically active transition metal complex catalyst having an aminophosphine-phosphinite ligand (Synlett., 1998, Vol. 10, pp1162), however, the catalyst was not always satisfactory in the asymmetric reaction of converting a carbonyl compound to a chiral alcohol compound.
Hence, a more effective catalyst that can be suitably used for industrial-scale production has been desired.
According to the present invention, an efficient catalyst for asymmetric production process is provided.
The present invention provides:
1. a chiral phosphine compound of formula (1): 
wherein R1 and R2 independently represent
an aryl or heteroaryl group, which may be substituted,
a saturated hydrocarbon group, which may be substituted, and
Ar group independently represents
an aryl or heteroaryl group, which may be substituted,
an aryloxy group, which may be substituted,
a saturated hydrocarbon group, which may be substituted, or
Ar groups on the same phosphorus atom are bonded to form an arylene, heteroarylene or alkylene group, which may be substituted, and
* represents an asymmetric carbon atom;
2. a transition metal complex of a chiral phosphine compound of formula: (1) as defined above;
3. a process for producing a chiral phosphine compound of formula (1) as defined above, which comprises reacting an optically active azetidine alcohol compound of formula (2): 
wherein R1, R2 and * represent the same as defined above, with a phosphine of formula (3):
Xxe2x80x94P(Ar)2xe2x80x83xe2x80x83(3),
wherein X represents a leaving group (e.g. a halogen atom, or the like.)
Ar represents the same as defined above;
4. an optically active azetidine alcohol compound of formula (4): 
wherein R1 and R2 independently represent
a saturated hydrocarbon group, which may be substituted, and
* represent the same as defined above; and
5. a process for producing an optically active organic compound, which comprises asymmetrically reducing a prochiral unsaturated compound with hydrogen in the presence of the transition metal complex of a compound of formula (1) as defined above.